Wood preservative compositions

Abstract

In general, the present disclosure is directed to a wood preservative composition. The wood preservative composition may be useful in inhibiting proliferation of wood decaying microorganisms. The wood preservative composition may include encapsulated 3-iodo-2-propynylbutylcarbamate (IPBC). The wood preservative compound may further include a succinate dehydrogenase inhibitor comprising penflufen. For instance, encapsulated IPBC and penflufen may be present in the wood preservative composition at a ratio of from about 1000:1 to about 1:50.

Description

WOOD PRESERVATIVE COMPOSITIONSCROSS-REFERENCE TO RELATED APPLICATION

[0001] The present application is related and has right of priority to U.S. Provisional Application No. 63 / 676,980 fded on July 30, 2024 in the United States Patent and Trademark Office and which is incorporated by reference in its entirety herein.BACKGROUND

[0002] Wood based products are subject to attack from a wide variety of organisms, including molds, fungi, and insects. As such, these organisms may cause the wood-based product’s wood to decay and reduce the product’s mass and structural integrity. Wood preservatives have been developed to combat microorganism attacks. Wood-based products may be treated with a wood preservative via applying the preservative directed to the surface, by dip, spray or brush, or by vacuum pressure immersion. During industrial application of preservatives, wood-based products are typically impregnated with the preservative treatment solution to achieve either shell or full cell type penetration into the substrate. A wood preservative treatment may have a significant bearing on the useful service life of the treated wood-based product.

[0003] There are a few wood preservatives commercially available that do not contain metal. In Europe and North America, available wood preservatives primarily include water-based IPBC by itself, a combination of IPBC and azole, or a combination of IPBC and quaternary ammonium compounds (QUATs). However, these options come with certain limitations. For instance, products containing IPBC alone are susceptible to degradation when exposed to heat and ultraviolet (UV) radiation. When it comes to the combination of IPBC and azole, a notable concern arises regarding the uncertainty surrounding the continued use of azoles in wood preservatives, particularly in the EU region. In the case of products combining IPBC and QUATs, a challenge arises from the presence of free amines in QUATs, which can destabilize IPBC and lead to formulation instability issues.

[0004] Accordingly, there is a need for stable, metal-free wood preservative compositions that are effective against various wood decay microorganisms, including fungi, molds, sapstain, and insects.SUMMARY

[0005] In general, the present disclosure is directed to a wood preservative composition. The wood preservative composition may be useful in inhibiting proliferation of wood decaying microorganisms as well as discoloration and disfiguration fungi, such as mold, mildew, and / or bluestain. In one example embodiment, the wood preservative composition may include encapsulated or controlled release 3-iodo-2-propynylbutylcarbamate (IPBC). The wood preservative compound may further include a succinate dehydrogenase inhibitor comprising penflufen. For instance, encapsulated or controlled release IPBC and penflufen may be present in the wood preservative composition at a ratio of from about 50:1 to about 1:50.

[0006] In an example embodiment, the wood preservative composition may comprise IPBC, a succinate dehydrogenase inhibitor comprising penflufen, and an insecticide. Encapsulated IPBC and the insecticide may be present in the composition at a weight ratio of from about 10:1 to about 1:10.

[0007] These and other features and aspects, embodiments and advantages of the present invention will become better understood with reference to the following description and appended claims.BRIEF DESCRIPTION OF THE DRAWINGS

[0008] A full and enabling disclosure of the present disclosure is set forth more particularly in the remainder of the specification, including reference to the accompanying figures, in which:

[0009] Figure 1 depicts a dose-response curve of penflufen and encapsulated IPBC and doseresponse matrix of penflufen and encapsulated IPBC combination.

[0010] Figure 2 depicts synergy scores at various ratios of penflufen: encapsulated IPBC.

[0011] Repeat use of reference characters in the present specification and drawings is intended to represent the same or analogous features or elements of the present invention.DETAILED DESCRIPTION

[0012] It is to be understood by one of ordinary skill in the art that the present discussion is a description of exemplary embodiments only, and is not intended as limiting the broader aspects of the present disclosure.

[0013] The present disclosure is generally directed to a metal-free wood preservative comprising a combination of encapsulated or controlled release 3-iodo-2-propynyl n-butyl-carbamate (TPBC) and a succinate dehydrogenase inhibitor (SDHI) comprising penflufen. Unexpectedly, the wood preservative composition disclosed herein displays significant synergy between the active components, providing enhanced biocidal efficacy against wood decay fungi, molds, sapstain, and insects. Surprisingly, the wood preservative composition may be utilized in the treatment of wood products, the resulting wood product exhibits improved properties against microorganisms that produce mold and / or sapstain on wood or wood products. Additionally, the wood preservative composition may exhibit less active leaching when utilized in treatment of wood products.

[0014] Wood preservative compositions disclosed herein may comprise an iodoalkynl compound, such as an iodoalkynl carbamate. The iodoalkynl carbamate, for instance, may generally have the following formula:in which m is 1 , 2 or 3; n is 1 , 2 or 3; and R is hydrogen (H); an unsubstituted or substituted alkyl, aryl, aralkyl alkylaryl, alkenyl, cycloalkyl, or cycloalkenyl or an alkoxy aryl all having from one to not more than 20 carbon atoms, and m and n may be the same or different.

[0015] Suitable R substituents for the iodoalkynyl carbamate compound include alkyls, such as methyl, ethyl, propyl, n-butyl, t-butyl, pentyl (amyl), hexyl, heptyl, octyl, nonyl, decyl, dodecyl, octadecyl, cycloalkyls, such as cyclohexyl, aryls, alkaryls and aralkyls, such as phenyl, benzyl, tolyl, cumyl, halogenated alkyls and aryls, such as chlorobutyl and chlorophenyl, and alkoxy aryls, such as ethoxyphenyl and the like. Thus, suitable carbamate compounds are selected from the group consisting of 3-iodo-2-propynyl butyl carbamate (IPBC), 3-iodo-2- propynyl hexyl carbamate (IPHC), 3-iodo -2-propynyl cyclohexyl carbamate (IPCC), 3-iodo-2- propynyl phenyl carbamate (IPPhC), 3-iodo-2-propynyl benzyl carbamate (IP Benzyl C), 3-iodo-2-propynyl propyl carbamate (IPPC), 4-iodo-3-butynyl propyl carbamate (IBPC), 3-iodo-2- propynyl-4-chloro phenyl carbamate (IPCIPhC), 3-iodo-2-propynyl-4-chloro butyl carbamate (IPC1BC) and mixtures thereof. In one example embodiment, the carbamate compound may be3-iodo-2-propynyl n-butyl-carbamate (IPBC).

[0016] The carbamate compound utilized herein may be encapsulated for controlled release. For instance, IPBC may be encapsulated so that IPBC is released over time. Published patent application WO 2010 / 148158 Al, which is incorporated by reference in its entirety, describes aprocess for the preparation of a sustained-release biocidal composition containing microencapsulated biocide, which comprises the steps of: (i) adsorbing the biocide onto an inert carrier and grinding to attain a desired particle size with a ratio of biocide to inert carrier in the range of about 1 : 99 to about 99: 1 ; (ii) optionally coating the biocide and inert carrier with an appropriate amine or imine compound or a water resistant film forming polymer, and dispersing the encapsulated biocide in an aqueous medium in the presence of a dispersing agent; (iii) adding at least one thickening agent to re-disperse the encapsulated biocide; and (iv) preparing an aqueous or solvent based sustained release biocide dispersion.

[0017] W.A. Ibrahim et aL, “Performance of Microencapsulated Fungicide in Exterior Latex Paint on Wood Substrate,” Pertanika, Vol. 12, No.3, 1989, pages 409-412, which is incorporated by reference in its entirety, relate to micro-encapsulated IPBC prepared by in-situ polymerization of crosslinking urea formaldehyde resin.

[0018] Wood preservative compositions disclosed herein may comprise a succinate dehydrogenase inhibitor. Generally, “succinate dehydrogenase inhibitor,” as used herein, refers to an active substance that inhibits succinate dehydrogenase in a mitochondrial respiration chain. In one example embodiment, the succinate dehydrogenase inhibitor may include a carboxamide compound. Suitable carboxamide compounds include carboxanilides, carboxylic morpholides, benzoic acid amides, and other carboxamides.

[0019] For instance, the carboxanilides may include benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, fluxapyroxad, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxy-carboxin, penthiopyrad, sedaxane, solatenol, tecloftalam, thifluzamide, tiadinil, 2- amino-4-methyl-thiazole-5-carboxanilide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3- difluoromethyl-1 -methyl- lH-pyrazole-4-carboxamide and N-(2-(l,3,3-trimethyl-butyl)-phenyl)- l,3-dimethyl-5-fluoro-lH-pyrazole-4-carboxamide.

[0020] The carboxylic morpholides may include, for instance, dimethomorph, flumorph, and pyrimorph.

[0021] The benzoic acid amides may include, for instance, flumetover, fluopicolide, fluopyram, and zoxamide.

[0022] The “other” carboxamides may include, for instance, carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofam, niacinamide, nicotienamide and N-(6-mcthoxy- pyridin-3-yl) cyclopropanecarboxylic acid amide.

[0023] In one example embodiment, the at least one succinate dehydrogenase inhibitor may be selected from a group consisting of flutolanil, isofetamid, flupyram, fluxapyroxad, penthiopyrad, boscalid, fenfuram, caboxin, thifluzamide, benzovindiflupyr, bixafen, fiirametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, solatenol, or a combination thereof. In one example embodiment, the succinate dehydrogenase inhibitor may be penflufen.

[0024] For instance, encapsulated IPBC and penflufen may be present in the wood preservative composition at a weight ratio of encapsulated IPBC and penflufen of from about 50:1 to about 1:50, such as a weight ratio of about 25:1 to about 1:25, such as a weight ratio of about 10:1 to about 1:10, such as a weight ratio of about 5:1 to about 1:5, or any range therebetween.

[0025] Wood preservative compositions disclosed herein may include encapsulated IPBC in combination with penflufen. Without wishing to be bound by theory, penflufen synergistically operate with IPBC to destroy and / or inhibit growth of a target microorganism, particularly at least one fungi. For instance, the wood preservative composition of the present disclosure can have an enhanced efficacy against one or more target microorganisms compared to a composition containing only a single biocidal again at the same concentration. In comparison to using either encapsulated IPBC or penflufen alone, for instance, the wood preservative composition of the present disclosure can display a fractional inhibitory concentration (FIC) index value of less than 1, such as less than about 0.9, such as less than about 0.8, such as less than about 0.7, such as less than about 0.6, when tested against various fungi.

[0026] Wood preservative compositions disclosed herein may include an insecticide. For instance, encapsulated IPBC and the insecticide may be present in the wood preservative composition at a weight ratio of encapsulated IPBC to the insecticide of from about 10:1 to about 1:10, such as a weight ratio of about 5:1 to about 1:5, or any range therebetween.

[0027] The insecticide may include, but are not limited to, a neonicotinoid, a pyrethroid, a phenylpyrazole, an avermectin, an organophosphate, a borate, a chitin synthesis inhibitor, an uncoupler of oxidative phosphorylation, an insect growth regulator, or a combination thereof.

[0028] In one example embodiment, the insecticide may be a pyrethroid. For instance, the pyrethroid may be selected from a group consisting of acrinathrin, allethrin, bioallethrin, barthrin, bifenthrin, bioethanomethrin, cyclethrin, cycloprothrin, cyfluthrin, cypermethrin, beta- cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, dimefluthrin, dimethrin, empenthrin, fenfluthrin, fenpirithrin, fenpropathrin, fenvalerate, esfenvalerate, flucythrinate, fluvalinate, tau-fluvalinate, furethrin, imiprothrin, metofluthrin, permethrin, biopemiethrin, transpermethrin, phenothrin, prallethrin, profluthrin, pyresmethrin, resmethrin, bioresmethrin, cismethrin, tefluthrin, terallethrin, tetramethrin, tralomethrin, transfluthrin, etofenprox, flufenprox, halfenprox, protrifenbute, silafluofen, or a combination thereof.

[0029] In one example embodiment, the insecticide may be a neonicotinoid. For instance, the neonicotinoid may be selected from a group consisting of (lE)-N-[(6-chloro-3- pyridinyl)methyl]-N'-cyano-N-methylethanimidamide (acetamiprid), (E)-l-[(2-chlorothiazol-5- yl)methyl] -3 -methyl-2-nitroguanidine (clothianidin), (2E)- 1 - [(6-chloro-3 -pyridinyl)methyl]-N - nitro-2-imidazolidinimine (imidacloprid), (lE)-N-[(6-chloro-3-pyridinyl)methyl]-N-ethyl-N'- methyl-2-nitro- 1 , 1 -ethenediamine (nitenpyram), tetrahydro-2-(nitromethylene)-2H- 1 ,3 -thiazine (nithiazine), (Z)-[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]cyanamide (thiacloprid), 3-[(2-chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro-4H-l,3,5-oxadiazin-4-imine (thiamethoxam), or a combination thereof.

[0030] In one example embodiment, the insecticide may be a borate. For instance, the borate compound may be disodium octaborate tetrahydrate (DOT).

[0031] In one example embodiment, the insecticide may be independently selected from the group consisting of imidacloprid, bifenthrin, fipronil, etofenprox, permethrin, cypermethrin, buprofezin, emamectin benzoate, or a combination thereof. In another example embodiment, the insecticide may be permethrin. In yet another example embodiment, the insecticide may be cypermethrin.

[0032] The wood preservative compositions disclosed herein are particularly effective against fungi and / or bacteria. Exemplary microorganisms may include one or more species from one or both of the following groups:

[0033] Fungi: Acremonium such as Acremonium strictum, Alternaria such as Alternaria tenuis or Alternaria alternata, Aspergillus such as Aspergillus niger or Aspergillus brasiliensis, Candida such as Candida albicans, Chaetomium such as Chaetomium globosum, Coniophora such as Coniophora puteana, Fibroporia radiculosa, Fusarium such as Fusarium solani, Geotrichum such as Geotrichum candidum, Gloeophyllum trabeum, Lentinus such as Lentinus tigrinus, Neolentinus lepideus, Penicillium such as Penicillium glaucum, Penicillium funiculosum or Penicillium pinophilum, Rhodotorula such as Rhodotorula rubra or Rhodotorula mucilaginosa, Rhodonia placenta, Stachybotrys such as Stachybotrys chartarum, Trametes such as Trametes versicolor, Trichoderma such as Trichoderma virens, Wolfiporia such as Wolfiporia cocos,' and

[0034] Insects: Reticultimermes such as Reticuliterm.es flavipes, Reticulitermes hesperus, Coptotermes such as Comitermes cumulans, Coptotermes formosanus, Crypto ter mes spp., Heterotermes such as Heterotermes ferox, Heterotermes paradoxus, Heterotermes vagus, or Hylotrupes such as Hylotrupes bajulus.

[0035] IPBC is not stable when exposed to ultraviolet light, heat, and severe chemical conditions. Degradation of IPBC may impact its performance against wood decay fungi and mold. Disclosed herein is a stable, wood preservative composition including penflufen and encapsulated IPBC. Surprisingly, the wood preservative composition disclosed herein has better performance and less active leaching.

[0036] Regardless of the form of the wood preservative composition, in one example aspect is diluted as discussed above, and used to treat a wood or cellulose based substrate. For instance, in one example aspect, the application of the wood preservative composition of the present disclosure to the wood or cellulose based substrate may be by one or more of dipping, deluging, spraying, brushing, or other surface coating means or by impregnation methods, e.g., high pressure or double vacuum impregnation into the body of the wood or other material. In one aspect, the method is impregnation under pressure.

[0037] Within this specification, embodiments have been described in a way that enables a clear and concise specification to be written, but it is intended and will be appreciated that embodiments may be variously combined or separated without departing from the disclosure. For example, it will be appreciated that all preferred features described herein are applicable to all aspects of the disclosure described herein.

[0038] In some example embodiments, the disclosure herein can be construed as excluding any element or process step that does not materially affect the basic and novel characteristics of the composition or process. Additionally, in some embodiments, the disclosure can be construed as excluding any element or process step not specified herein.

[0039] As used herein, the temis “about,” “approximately,” or “generally,” when used to modify a value, indicates that the value can be raised or lowered by 10% and remain within the disclosed aspect, such as 7.5%, such as 5%, such as 4%, such as 3%, such as 2%, such as 1%, or any ranges or values therebetween. Moreover, the term “substantially free of’ when used to describe the amount of substance in a material is not to be limited to entirely or completely free of and may correspond to a lack of any appreciable or detectable amount of the recited substance in the material. Thus, e.g., a material is “substantially free of’ a substance when the amount of the substance in the material is less than the precision of an industry-accepted instrument or test for measuring the amount of the substance in the material. In certain example embodiments, a material may be “substantially free of’ a substance when the amount of the substance in the material is less than 10%, less than 9%, less than 8%, less than 7%, less than 6%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, or less than 0.1% by weight of the material. It will be understood that, in certain example embodiments, the compositions described herein may be substantially free of any substance not specifically recited.

[0040] As used in this application and in the claims, the singular forms “a,” “an,” and “the” include the plural forms unless the context clearly dictates otherwise. Additionally, the temi “includes” means “comprises.” The methods and compositions of the present disclosure, including components thereof, can comprise, consist of, or consist essentially of the essential elements and limitations of the embodiments described herein, as well as any additional or optional ingredients, components or limitations described herein or otherwise useful in nutritional compositions.

[0041] Unless otherwise indicated, all numbers expressing quantities of ingredients, properties such as molecular weight, percentages, and so forth, as used in the specification or claims are to be understood as being modified by the term “about.” Accordingly, unless otherwise indicated, implicitly or explicitly, the numerical parameters set forth are approximations that may depend on the desired properties sought and / or limits of detectionunder standard test conditions / methods. When directly and explicitly distinguishing embodiments from discussed prior art, the embodiment numbers are not approximates unless the word “about” is recited.

[0042] As used herein, “optional” or “optionally” means that the subsequently described material, event or circumstance may or may not be present or occur, and that the description includes instances where the material, event or circumstance is present or occurs and instances in which it does not. As used herein, “w / w%” and “wt%” means by weight as a percentage of the total weight or relative to another component in the composition.

[0043] The phrase “effective amount” means an amount of a compound that promotes, improves, stimulates, or encourages a response to the particular condition or disorder or the particular symptom of the condition or disorder.

[0044] Although the disclosure is illustrated and described herein with reference to specific embodiments, the disclosure is not intended to be limited to the details shown. Rather, various modifications may be made in the details within the scope and range of equivalents of the claims and without departing from the disclosure.EXAMPLESExample 1

[0045] The susceptibility of typical molds and sapstian fungi to penflufen and encapsulated IPBC was determined using checkerboard assay. This checkerboard assay is one way of measuring the effect of biocidal combination. Varying concentrations of penflufen and encapsulated IPBC is dispersed along the columns and rows to allow for the determination of minimum inhibitory concentration (MIC) for each biocide in combination. The starting concentration is around 2 ppm and is diluted down in 1.5-fold or 2-fold gradient. The percent inhibition is calculated by optical density via OD600 measurements taken after 6 days of growth in 96-well format. The dose response curve for penflufen and encapsulated IPBC and doseresponse matrix of combination is shown in Figure 1. Given our understanding about the different mechanisms of action between penflufen and IPBC, Bliss independence principle is more appropriate in this test. The synergistic interaction of penflufen in combination with encapsulated IPBC is presented using a heat map or surface plot based on the percent excess the Bliss prediction using the average response measures at each combination dose (Figure 2).

[0046] These and other modifications and variations to the present disclosure may be practiced by those of ordinary skill in the art, without departing from the spirit and scope of the present disclosure, which is more particularly set forth in the appended claims. In addition, it should be understood that aspects of the various embodiments may be interchanged both in whole or in part. Furthermore, those of ordinary skill in the art will appreciate that the foregoing description is by way of example only, and is not intended to limit the disclosure so further described in such appended claims.

Claims

WHAT IS CLAIMED:

1. A wood preservative composition comprising: encapsulated 3-iodo-2-propynylbutylcarbamate (IPBC); a succinate dehydrogenase inhibitor comprising penflufen; and an aqueous carrier, wherein the weight ratio of encapsulated IPBC to penflufen is about 50: 1 to about 1:50.

2. The wood preservative composition of claim 1, wherein the weight ratio of encapsulated IPBC to penflufen is about 25: 1 to about 1:25.

3. The wood preservative composition of claim 1, wherein the weight ratio of encapsulated IPBC to penflufen is about 10: 1 to about 1:

104. The wood preservative composition of claim 1, wherein the weight ratio of encapsulated IPBC to penflufen is about 5: 1 to about 1 :5.

5. The wood preservative composition of claim 1, further comprising an insecticide.

6. The wood preservative composition of claim 5, wherein the insecticide is independently selected from the group consisting of a neonicotinoid, a pyrethroid, a phenylpyrazole, an avermectin, a chitin synthesis inhibitor, an uncoupler of oxidative phosphorylation, an insect growth regulator, or a combination thereof.

7. The wood preservative composition of claim 5, wherein the insecticide is independently selected from the group consisting of imidacloprid, bifenthrin, fipronil, etofenprox, permethrin, cypermethrin, buprofezin, emamectin benzoate, or a combination thereof.

8. The wood preservative composition of claim 5, wherein the insecticide comprises permethrin.

9. The wood preservative composition of claim 5, wherein the insecticide comprises cypermethrin.

10. The wood preservative composition of claim 5, wherein encapsulated TPBC and the insecticide are present in the composition at a weight ratio of from about 10: 1 to about 1 : 10.

11. The wood preservative composition of claim 5, wherein encapsulated IPBC and the insecticide are present in the composition at a weight ratio of from about 5 : 1 to about 1 :5.

12. A wood preservative composition comprising: encapsulated 3-iodo-2-propynylbutylcarbamate (IPBC); a succinate dehydrogenase inhibitor comprising penflufen; and an insecticide, wherein the weight ratio of encapsulated IPBC to the succinate dehydrogenase inhibitor is about 50:1 to about 1 :50, wherein encapsulated IPBC and the insecticide are present in the composition at a weight ratio of from about 10: 1 to about 1 : 10.

13. The wood preservative composition of claim 12, wherein the weight ratio of encapsulated IPBC to penflufen is about 25: 1 to about 1 :25.

14. The wood preservative composition of claim 12, wherein the weight ratio of encapsulated IPBC to penflufen is about 10: 1 to about 1 : 1015. The wood preservative composition of claim 12, wherein the weight ratio of encapsulated IPBC to penflufen is about 5: 1 to about 1 :5.

16. The wood preservative composition of claim 12, wherein the insecticide is independently selected from the group consisting of a neonicotinoid, a pyrethroid, a phenylpyrazole, an avermectin, a chitin synthesis inhibitor, an uncoupler of oxidative phosphorylation, an insect growth regulator, or a combination thereof.

17. The wood preservative composition of claim 12, wherein the insecticide is independently selected from the group consisting of imidacloprid, bifenthrin, fipronil, etofenprox, permethrin, cypermethrin, buprofezin, emamectin benzoate, or a combination thereof.

18. The wood preservative composition of claim 12, wherein the insecticide comprises permethrin.

19. The wood preservative composition of claim 12, wherein the insecticide comprises cypermethrin.

20. The wood preservative composition of claim 12, wherein encapsulated IPBC and the insecticide are present in the composition at a weight ratio of from about 5 : 1 to about 1 :5.

21. A wood-based product treated with the wood preservative composition of any one of claims 1-12.

22. A wood preservative composition comprising: controlled release 3-iodo-2-propynylbutylcarbamate (IPBC); a succinate dehydrogenase inhibitor comprising penflufen; and an aqueous carrier, wherein the weight ratio of controlled release IPBC to penflufen is about 50: 1 to about 1 :50.

23. A method of treating a wood-based product with the wood preservative composition of any one of claims 1-12.

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